Hollywood Flashback: Oprah and Trump First Crossed Paths in 1988

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Donald Trump and Oprah Winfrey sat next to promoter Don King (far right) at the Mike Tyson-Michael Spinks fight in Atlantic City on June 27, 1988, two months after Trump was a guest on her daytime talk show.

The media mogul and now-president have a long history going back even before the recent speculation that she could run against him in 2020, including his nine appearances on her former talk show.

Oprah Winfrey, 63, and Donald Trump, 71, have a history that stretches back long before the recent speculation — ignited by her fiery Golden Globes speech — that she could challenge him in the 2020 election.

Just two years after her talk show went national, the future media mogul had the future president of the United States — whose fame had risen after the publication of his 1987 book, The Art of the Deal — appear as a guest. (When The Oprah Winfrey Show launched Sept. 8, 1986, on L.A.'s KABC as a replacement for Tom Snyder and a new challenger to Phil Donahue's daytime dominance, THR's review said it was "heavily slanted towards the realm of pop psychology" and was "not exactly the apogee of intellectualism, but it doesn't bill itself as such.")

On the April 25, 1988, show, Winfrey asked Trump about full-page newspaper ads he'd taken out attacking U.S. foreign policy. When she said their content sounded like "political presidential talk," Trump replied, "Probably not, but I do get tired of seeing the country get ripped off." (He stressed topics like allies taking trade advantage of the U.S. and not paying their fair share for defense — the same issues he ran on in the 2016 election.)

When Winfrey asked if he thought he'd win a presidential bid, Trump answered: "Well, I don't know, I think I'd win. I'll tell you what: I wouldn't go in to lose. I've never gone in to lose in my life." And while his affection might diminish if Winfrey runs against him in 2020 (he appeared on her show nine times), when asked by Larry King on CNN in 1999 if he "had a vice presidential candidate in mind," Trump replied: "Oprah. I love Oprah. Oprah would always be my first choice."

Asked Jan. 9 in the Cabinet Room how he felt about a Trump-Winfrey matchup, the president said, "I'd beat Oprah … [but] I don't think she's going to run." 

This story first appeared in the Jan. 17 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.